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Vacation rentals in Henderson

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Quick stats about vacation rentals in Henderson

  • Total vacation rentals

    Explore 30 vacation rentals in Henderson

  • Nightly prices starting at

    Henderson vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 540 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Henderson vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Henderson rentals

  • 4.7 Average rating

    Henderson stays receive an average rating of 4.7 out of 5 from guests

Top-rated vacation rentals in Henderson

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
Home in Evansville

Historic Haynie's Corner Hideout

Warm, cozy and spacious historic home located right near the vibrant Haynie's Corner. Features original art from local artists as well as others. Inviting living spaces, fully stocked kitchen and coffee bar, large dining room and cushy bedrooms all make for a great place to relax, unwind and enjoy your stay away from home. Work area, gaming nook, comfortable sun porch, side yard fire pit and lounge area take your stay to the next level! We look forward to creating a wonderful experience for you.

4.94 out of 5 average rating, 101 reviews
Top guest favourite
Apartment in Henderson

The Mint Julep! Upstairs 3BD/2BA - Next to Brewery

Book your stay at The Mint Julep and experience Henderson like a local. Fresh vibes, classic charm, and a stay worth toasting. You are "mint" to make memories at The Mint Julep. Welcome to The Mint Julep, a stylish and spacious upstairs retreat in the heart of Henderson, Kentucky! This 3-bedroom, 2-bath rental is perfectly located adjacent to Henderson Brewing Co., near Holy Name Church, and just a short walk from downtown restaurants, shops, riverfront attractions, and seasonal festivals.

5.0 out of 5 average rating, 13 reviews
Guest favourite
A spacious living room features two comfortable sofas and a single armchair arranged around a round coffee table. Large windows allow natural light to fill the area, and a decorative area rug adds a touch of warmth to the hardwood floor.
Loft in Henderson

The Nest - Huge Loft in Downtown Henderson

Welcome to The Nest, Henderson's finest loft! This Victorian 1800 sq. ft. loft is newly renovated, fully furnished and nicely appointed in the heart of Downtown Henderson. The huge living room is perfect to meet friends, watch TV, cook, or just gaze out the massive windows. The Master Room, Reading Room (featuring a queen Murphy bed), fully equipped Kitchen, and Private Patio are quiet spaces to relax, work, prepare a meal, or plan your day. Parking, fast wifi, and washer/dryer all included!

4.99 out of 5 average rating, 106 reviews
Guest favourite
A contemporary living area features two patterned armchairs beside a small round table with a decorative lamp. Abstract artwork adorns the brick wall, while a textured rug adds comfort underfoot. Soft, ambient light enhances the inviting space.
Loft in Evansville

The Cooper I on Franklin (The Ashby Collection)

Right in the heart of Franklin Street! All the “city feels” in this contemporary walk up loft! We provide all the pleasures, perks and pampering of a hotel, but in a fully-furnished private luxury residence. Just steps away from incredible restaurants, bars, pubs, live music, and specialty boutiques. Once you’ve arrived at The Cooper, grab a seat at our window bar overlooking Historic Franklin Street! We have equipped you with everything from a well appointed kitchen to a fabulous hot tub!

4.98 out of 5 average rating, 126 reviews
Top guest favourite
The exterior of the cottage showcases a welcoming blue facade with white trim. A covered porch features a comfortable swing, and large windows provide ample natural light. Lush green trees frame the peaceful setting, enhancing the cottage's serene ambiance.
Home in Henderson

Little House on the River

This gem is nestled on the riverbank, offering you a tranquil getaway with stunning water views and quiet surroundings. Our cozy cottage is perfect for couples or solo adventurers. You'll enjoy a blend of rustic charm and contemporary amenities. The open-concept living area features large windows that flood the space with natural light, offering uninterrupted views of the river. Situated on a peaceful, dead end street and just a short drive to local attractions, shops, and restaurants.

5.0 out of 5 average rating, 56 reviews
Top guest favourite
Cabin in Dixon

Crouse’s North Ninety Lake House

If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

4.96 out of 5 average rating, 346 reviews
Guest favourite
The interior showcases a warm, wooden design with vaulted ceilings and exposed beams. A modern television is mounted on the wall above a stone fireplace, while a cozy seating area is arranged with a dark sofa and wooden coffee table. The space is well-lit and inviting.
Cabin in Corydon

The Geneva Cabin

The Geneva Cabin is one of a kind (not in the woods) and has everything you need to enjoy whatever occasion brings you to the area. Located less than 2 miles from the wildlife refuge, 10 min to downtown Henderson, 7 mi to I-69 the property sits in the middle of a quiet dead-end street. Right in the middle of anywhere anyway your journey takes you. 55” TV, sofa bed and recliner in living room, WIFI, washer & dryer. Fully equipped kitchen. Large parking area.

4.93 out of 5 average rating, 136 reviews
Top guest favourite
The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.
Cabin in Dixon

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

4.91 out of 5 average rating, 556 reviews
Guest favourite
The cabin is showcased with a modern architectural design, featuring a wooden facade and large windows that allow for natural light. The structure sits on a grassy area, with a clear blue sky enhancing the overall appearance.
Cabin in Robards

REINE CABIN at Farmer and Frenchman

EAT. TASTE. STAY. Year round view, seasonal flavor. The property features a winery/cafe, a vineyard, walking trails, and a 360 view of countryside. Created in the spirit of rustic elegance, the Cabin's lavish accents are sure to impress. Enjoy dinner in the cafe, walk the trails, snuggle in for the night, order breakfast in bed and a morning yoga session on the patio. Enjoy the ambiance of Kentucky's agrarian heritage with modern and stylish amenities.

4.93 out of 5 average rating, 127 reviews
Guest favourite
A historic brick building stands on a cobblestone street, framed by mature trees and shrubs. The entrance features a set of stairs leading to double doors adorned with decorative glass. A lamppost adds charm to the inviting outdoor space.
Apartment in Evansville

Victorian 1 Bedroom Guesthouse Apt on 1st Street

This one-bedroom / one-bathroom apartment features high ceilings and exposed brick and is attached to your host’s home - a Victorian townhouse on one of Evansville’s historic cobblestone streets. Enjoy easy self-check-in and a location that is centrally located near the Ohio River, Downtown Evansville, and Haynie’s Corner neighborhoods. The Ford Center, Bally’s Casino, and many of Evansville’s best restaurants and bars are all a short walk away.

4.95 out of 5 average rating, 278 reviews
Top guest favourite
Home in Evansville

Rooftop Deck + 100" Theater | Downtown Evansville

Step into history at the Dr. J.R. Mitchell House (1909) — Evansville's first animal clinic, now a modern industrial retreat in the heart of downtown. Exposed brick, a private rooftop deck with city views, a 100-inch projector theater with surround sound, and a jetted tub for two. Walk to the riverfront, Ford Center, and Main Street dining. Fast WiFi and a dedicated workspace make it an easy home base for business and medical travelers.

4.96 out of 5 average rating, 279 reviews
Top guest favourite
Home in Corydon

The Farm

Step away from the fast pace of daily life and enjoy family, friends and the peace of country living. Secluded modern farm house, that began as a log cabin, situated on approximately 100 acres of crop fields and includes a scenic lake. This property has been in our family for over 100 years. It has been lovingly furnished and decorated for a one of a kind stay. We want our guests to unplug, refresh, and renew.

4.96 out of 5 average rating, 236 reviews

Popular amenities for Henderson vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Henderson

Guest favourite
A four-poster bed with a floral patterned duvet is positioned against a light grey wall, complemented by two decorative pillows. Soft lighting from a bedside lamp creates a cozy ambiance, while yellow curtains frame the window, adding warmth to the space.
Apartment in Henderson

Suburban Chateau (No cleaning fee)

4.93 out of 5 average rating, 88 reviews
Top guest favourite
A charming house stands amidst tall trees, softly illuminated by outdoor lighting in the evening. The two-story structure features a spacious deck and large glass doors, blending seamlessly with the surrounding woodland. A gravel path leads up to the entrance, enhancing the tranquil setting.
Home in Webster County

Newly Listed! Secluded 3 BR house in the Woods!

5.0 out of 5 average rating, 51 reviews
Superhost
Apartment in Henderson

Henderson Haven | KING 2BD/1BA Newly Renovated Apt

4.66 out of 5 average rating, 50 reviews
Top guest favourite
Apartment in Evansville

Family ready 4BR apt l King suite l DT adjacent

5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Evansville

Clean, Modern Space Near Hospitals & Campus

4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Evansville

Large 5BR + Game Room + Firepit, Prime Location

4.95 out of 5 average rating, 21 reviews
Top guest favourite
Aerial view of a spacious home surrounded by lush greenery and a serene lake. The property features a well-maintained lawn, a circular driveway, and a wooden fence. Nearby homes are visible along the waterfront, enhancing the sense of a peaceful community.
Home in Evansville

Lakeview Home by the Ball Fields

4.98 out of 5 average rating, 49 reviews
Top guest favourite
Home in Calhoun

The Nest

4.97 out of 5 average rating, 65 reviews

When is the best time to visit Henderson?

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Frequently Asked Questions

  • What are the best places to stay in Henderson?

    Stays around downtown Henderson are popular for walkable access to dining, shops, and river views. Other guests look for accommodations near John James Audubon State Park for a more nature–immersed experience.

  • What are the best things to do in Henderson with kids?

    Kids can explore the nature center at John James Audubon State Park, enjoy playgrounds, or participate in scavenger hunts and family-friendly events. Local museums and riverfront walks are popular for all ages.

  • What are some of the best things to do in Henderson?

    Explore nature trails at John James Audubon State Park, visit local art exhibits, or take in river views along the waterfront. The city also has shops, historic sites, and seasonal community events.

  • How is the weather in Henderson?

    Henderson has cold winters ranging from 26–42°F (-4–5°C) and warm, often humid summers near 88°F (31°C). Spring and fall bring milder temperatures and can be wetter, so packing layers and a rain jacket is helpful year-round.

  • When is the best time to visit Henderson?

    Late spring and early autumn are often recommended for milder temperatures and outdoor events. Summer brings warm weather and frequent community gatherings, while winter is quieter with cool, crisp air.

  • What are the best places to visit in Henderson?

    John James Audubon State Park, the city's riverwalk, and area museums are frequently suggested for visitors. Downtown Henderson is known for historic architecture and locally owned businesses.

  • What are some hiking trails in Henderson?

    John James Audubon State Park has several forested trails, including easy loops and slightly steeper paths with birdwatching opportunities. Check local trail maps for options that fit your pace and interests.

  • What are some family activities we can do in Henderson?

    Families often explore the nature center and playgrounds at John James Audubon State Park, join hands-on museum exhibits, or take part in community festivals. The riverfront features wide paths for walks or picnics together.

  • What are some of the best day trip ideas from Henderson?

    Guests can explore nearby state parks, visit small towns renowned for antique shops, or experience museums highlighting regional art and music. Outdoor recreation areas around the region feature lakes, wildlife viewing, and hiking.

  • Are there any pet friendly accommodations available in Henderson?

    Many accommodations in Henderson are pet friendly, with hosts typically describing their specific policies in the listing. Area parks and nearby trails also make it convenient for guests traveling with animals to get outside together.

  • What are some local tips for visiting Henderson?

    Consider bringing layers, as the weather shifts with the season. Locals often suggest exploring early in the day for quieter parks, trying the weekly farmers market, and asking about rotating art or music events during your stay.

  • What is Henderson known for?

    Henderson is known for its riverfront setting, John James Audubon State Park, and locally rooted arts and music traditions. The city often draws visitors for its festivals, outdoor recreation, and historic downtown.

  • What are the best hidden gems to explore in Henderson?

    Henderson has quiet riverfront parks, small museums, and locally rooted art galleries that are often less crowded. Exploring scenic overlooks or family–operated shops around downtown can reveal unique stories and local history.

  • What are the best foods to try in Henderson?

    Henderson has locally inspired barbecue, river fish dishes, and homemade pies that are frequently suggested. You can also explore traditional Southern cooking at family-run diners and seasonal produce at farmers markets.

  • What should I bring for a trip to Henderson?

    Pack comfortable walking shoes, layers for changing temperatures, and a light rain jacket. In warmer months, sunscreen and a refillable water bottle are useful for outdoor activities.

  • What is the nightlife in Henderson like?

    Henderson has live music venues, casual bars, and spots with local food or open mic nights, mainly centered around downtown. The scene is relaxed, focusing on music, food, and conversation.

  • What are the most popular events or festivals in Henderson?

    The W.C. Handy Blues and Barbecue Festival, held in early summer, is one of Henderson's most popular events. The city also hosts arts festivals and seasonal celebrations in its parks and downtown.

  • Are there family friendly vacation rentals in Henderson?

    Many vacation rentals in Henderson are geared toward families, with features like kitchens, multiple bedrooms, and easy access to parks. Listings often highlight nearby playgrounds, walking trails, or kid-friendly activities.